Tetrabutylammonium Fluoride → 3-Hydroxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine

HRID 891607Notes

Reaction equation

HRID 891607 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[O:29])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222430293-t-Butyldiphenylsilyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine

Product 1

HCID 222429433-Hydroxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (607 mg, 1.20 mmol) (obtained as described in Reference Example 27(1)) in anhydrous tetrahydrofuran (25 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.40 ml, 1.40 mmol) in an ice bath, and the mixture was stirred at room temperature for 1 hour. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate→ethyl acetate:methanol (9:1) as the eluant to afford 3-hydroxy-1-(4-piperidinocarbonyl-1,3-thiazol-2-yl)azetidine (310 mg, yield 97%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-be131fc7a06b44a497d567614053d490
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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